1. Field of the Inventive Subject Matter
The inventive subject matter relates to novel synthetic processes which use a multifunctional compound (the “TERMINI compound”) having a masked or protected functional group, wherein the TERMINI compound is capable of quantitatively and irreversibly interrupting a living polymerization or a chain organic reaction. After deprotection or demasking of the functional group of the TERMINI compound, the same living polymerization or organic reaction resumes with 100% efficiency, or a different living polymerization or organic reaction resumes with 100% chemoselectivity, respectively. Once incorporated into a growing molecule, the TERMINI compound generates a branching point upon resumption of the polymerization or reaction.
2. Background
It is expected that dendritic macromolecules will have increasing future importance in such diverse fields as nanoelectronics, for example electronics based on organic thin-film materials, and nanobiology. Presently, there are no simple, efficient, and cost effective processes for the synthesis of dendritic macromolecules. Current methods are expensive and not fully selective.
The general state of the patent art relating to dendritic polymers, and their uses, is described in the following U.S. patents.
U.S. Pat. No. 5,731,095 to Milco, et al., issued Mar. 24, 1998, discloses water-soluble or water-dispersible fluorine-containing dendritic polymer surfactants.
U.S. Pat. No. 5,886,110 to Gozzini, et al. issued Mar. 23, 1999, discloses branched, dendrimeric macromolecules having a central nucleus and a series of polyoxaalkylene chains that radiate from the nucleus and spread into the surrounding space, branching in a cascade fashion until the desired size results.
U.S. Pat. No. 6,020,457 to Klimash, et al. issued Feb. 1, 2000, discloses dendritic polymers containing disulfide functional groups which are essentially inert under non-reducing conditions, but which form sulfhydryl groups upon being subjected to a reducing agent, and their uses in the formation of differentiated dendrimers, formation of binding reagents for diagnostics, drug delivery, gene therapy and magnetic resins imaging, and in the preparation of self-assembled dendrimer monolayers on quartz crystal resonators to provide dendrimer-modified electrodes which are useful for detecting various ions or molecules.
U.S. Pat. No. 6,077,500 to Dvornic, et al., issued Jun. 20, 2000, discloses higher generation radially layered copolymeric dendrimers having a hydrophilic poly(amidoamine) or a hydrophilic poly(propyleneimine) interior and a hydrophobic organosilicon exterior, and their uses for delivering active species for use in catalysis, pharmaceutical applications, drug delivery, gene therapy, personal care, and agricultural products.
U.S. Pat. No. 6,136,921 to Hsieh, et al., issued Oct. 24, 2000, discloses a coupled polymer which is prepared by reacting a living alkali metal-terminated polymer with a coupling agent, having good rubbery physical properties, transparency, and wear resistance.
U.S. Pat. No. 6,312,809 to Crooks, et al., issued Nov. 6, 2001, discloses a substrate having a dendrimer monolayer film covalently bonded to the surface, and uses as a chemically sensitive surface, such as in chemical sensors.
The prior art has been ineffective in developing simple, efficient, and cost effective processes for the synthesis of dendritic macromolecules. Applicant has developed methods for the synthesis of complex chemical compounds with the shape perfection required to act as self-organizing and self-assembling building blocks to generate supramolecular objects in both novel and predictable structural lattices. When a supramolecular object exhibits an internal ordered structure rather than a micelle-like structure, the retrostructural analysis of the lattice enables the formulation of a primary structure-activity relationship that provides molecules with designed functions. Applicant has further found that novel dendritic macromolecules may be simply, efficiently, and cost effectively synthesized by the inventive methods. In particular, Applicant has developed new methods for the synthesis of complex molecular and macromolecular chemical compounds by a combination of living polymerization reactions and TERMINI synthesis.